✅ Toby's Takeaway 🤖 Exercises 📹 Video 💡Big Ideas 💬 Best Quotes 🛒 Buy on Amazon
📚 Should You Read This?
Toby's Rating: 6/10
How To Know Everything by Elke Wiss is a compelling guide to mastering the art of asking questions, rooted in Socratic philosophy. This book is an excellent entry for leaders who want to foster deeper conversations, encourage critical thinking, and build collaborative environments. Wiss presents practical tools for improving intellectual humility and curiosity, skills vital for problem-solving and innovation. This book offers practical ideas to enhance decision-making and team dynamics.
✅ Toby's Top Takeaway From How to Know Everything by Elke Wiss
Long-time readers of this newsletter do not need convincing.
Great leaders ask great questions.
I've shared countless book summaries that all reinforce the same idea.
The simple act of asking questions is much more complicated than you'd think.
And let's be clear.
I'm not talking about those fake, crappy questions that come easy to us all.
Questions like "should?", "could?", "would?"
I mean, the tough questions. Those that make you start sweating just thinking about asking it.
I've spent years learning to build a habit of asking rather than telling, gaining the confidence and competence to ask powerful questions when they matter most.
This week, I learned from Elke Wiss why asking questions is so bloody hard.
In How To Know Everything, Elke shares six reasons:
Human Nature: Talking about yourself feels so much nicer than asking questions.
Fear of Asking: Posing a question can be a scary proposition.
Scoring Points: An opinion makes more of an impression than a question.
Lack of Objectivity: Our ability to reason objectively is in decline.
Impatience: We think asking good questions is a waste of time.
Lack of competence: Nobody teaches us how.
To overcome these barriers, I've learned a simple technique.
I stole it from James Clear, author of Atomic Habits.
Make asking questions:
Easy
Obvious
Attractive
Satisfying
When you do that, over time, you build the questioning habit.
It turns out that a very jazzy name for this leadership style is practical philosophy.
And who doesn't want to be a philosopher?
🤖 Turn This Book Into Action
Despite reading this book, I still have a problem. I’m not converting the knowledge into action. To solve this problem, I’m turning to the solution everyone is looking for: artificial intelligence. I’ve developed a set of AI tools to turn knowledge into action.
💡 3 Big Ideas From How to Know Everything by Elke Wiss
The Power of Questions - Good questions invite exploration and deepen understanding, unlike statements that can shut down dialogue. Wiss encourages leaders to use thoughtful inquiry to challenge assumptions, uncover new perspectives, and foster collaborative thinking by focusing on why, how, and what if leaders can inspire creativity and problem-solving within their teams.
Cultivate Intellectual Humility - Elke highlights the importance of admitting "I don't know" as a gateway to growth. Leaders who embrace uncertainty and seek diverse viewpoints create environments where learning thrives. This mindset reduces defensiveness and promotes an open exchange of ideas, which is essential for navigating complex challenges.
Deep Conversations Foster Connection - Engaging in meaningful dialogues requires active listening and genuine curiosity. Elke suggests that leaders adopt a "you-first" approach, prioritising others' perspectives before sharing their own. This creates a shared understanding and strengthens relationships, which is key to building trust and collaboration in teams.
💬 Best Quotes From How to Know Everything by Elke Wiss
We are afraid to ask pertinent yet potentially awkward questions that might make someone feel uncomfortable. Yet often, these are the very questions that lead to a genuine connection because so much of what matters in life is located in that vulnerable zone.
We are too quick to assume someone would be reluctant to respond to a question.
Reasons why people don't ask questions:
HUMAN NATURE: Talking about yourself feels so much nicer than asking questions.
FEAR OF ASKING: Posing a question can be a scary proposition.
SCORING POINTS: An opinion makes more of an impression than a question.
LACK OF OBJECTIVITY: Our ability to reason objectively is in decline.
IMPATIENCE: We think asking good questions is a waste of time.
LACK OF COMPETENCE: Nobody teaches us how.
In her book Braving the Wilderness, Brent Brown writes:
I can't remember a time last year when someone asked me about an issue and I didn't weigh in with an opinion. Even if I didn't know enough about it to be Insightful or even conversational (ad) in a fitting-in culture - at home, at work, or in our larger community curiosity is seen as a weakness, and asking questions equates to antagonism rather than being valued as learning
Two monologues do not add up to a dialogue.
One of Socrates's rules of conversation is to speak briefly and concisely. In the dialogue with Protagoras, as described in Hans Bolten's article "The Socratic dialogue as a tool for team reflection; Socrates asks his conversation partner to stop indulging in incomprehensible monologues, claiming he simply cannot follow them.:
SOCRATES: Protagoras, I have a wretched memory, and when anyone makes a long speech to me I never remember what they are talking about. As then, if I had been deaf, and you were going to converse with me, you would have had to raise your voice; so now, having such a bad memory, I will ask you to cut your answers shorter, if you would take me with you.
PROTAGORAS: What do you mean? How am 1 to shorten my answers? Shall I make them too short?
SOCRATES: Certainly not.
PROTAGORAS: But short enough?
SOCRATES: Yes.'
When it comes to confrontation, we cling to quite a few assumptions:
Confrontation leads to conflict - the other person will probably feel hurt by my question, have no desire to answer it and is bound to respond defensively.
Confrontation creates tension - it jeopardises the relationship.
I only have the right to confront someone if I'm very knowledgeable about the subject at hand and believe I know more about it than they do.